Greatest Hits Main cast, played by Kelsea Ballerini Episode 1x01: 1980-1985 (Jun 30, 2016) Episode 1x02: 1995-2000 (Jul 7, 2016) Episode 1x03: 1985-1990 (Jul 14, 2016) Episode 1x04: 1990-1995 (Jul 21, 2016) Episode 1x05: 2000-2005 (Jul 28, 2016) Episode 1x06: Live Finale: 1980-2005 (Aug 4, 2016)